I wear flats with my narrower boot cuts. I'm 5'1". The pants have to be the right length so the bottoms almost graze the floor in the back. The shape and width of the toe must be just right...sometimes it helps if the shoe is lower cut in the front. Grandma shoes that cover the whole top of your foot might not work.

I am thin, so wearing any kind of heel probably takes away from my shape if I am wearing pants.